Hydrochloric Acid → HCID 21449478, compound

HRID 596995Notes

Reaction equation

HRID 596995 reaction equation
[CH:1]1([CH:6]2[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[C:7]2=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>O1CCCC1.C1C=CC=CC=1>[CH:1]1([CH:6]2[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[CH:7]2[OH:18])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21449495HCID 21449495, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 21449478HCID 21449478, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2-cyclopentyl-5-hydroxy-6,7-dichloro-1-indanone (8.55 g., 0.03 mole) in tetrahydrofuran (100 ml.) under nitrogen is added dropwise 70% sodium bis-(2-methoxyethoxy)-aluminum hydride in benzene (10 ml.) in tetrahydrofuran (30 ml.) over a ten minute period at 10°-15° C. The reaction mixture is stirred at 25° C. for 3 hours, cooled to 10° C., very slowly treated with 10% hydrochloric acid until frothing ceases, then with 20% hydrochloric acid until acidic. The tetrahydrofuran is decanted from a pasty residue, evaporated to dryness and the residue triturated with benzene to give 7.2 g. of 2-cyclopentyl-6,7-dichloroindan-1,5-diol which melts at 158°-160° C. after crystallization from benzene.

Workup

  1. temperaturecooled to 10° C.
  2. customThe tetrahydrofuran is decanted from a pasty residue
  3. customevaporated to dryness
  4. customthe residue triturated with benzene
  5. customto give 7.2 g
  6. customof 2-cyclopentyl-6,7-dichloroindan-1,5-diol which melts at 158°-160° C. after crystallization from benzene

Sources & evidence

ORD record
ord-710eb2419daa4a24872e5e137ba58eac
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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